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  • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
  • C07D491/04—Ortho-condensed systems
  • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Definitions

• the present invention relates to a photoelectric conversion element, an image sensor, an optical sensor, and a compound.
• Patent Document 1 discloses a compound applied to a photoelectric conversion element.
• the present inventor investigated photoelectric conversion elements using the compounds disclosed in Patent Document 1, etc., and found that they could not meet the current required level of manufacturing suitability and that further improvements were necessary. did.
• an object of the present invention is to provide a photoelectric conversion element with excellent manufacturing suitability. Another object of the present invention is to provide an image sensor, an optical sensor, and a compound.
• the present inventors have found that the above-mentioned problems can be solved by using a compound having a predetermined structure in a photoelectric conversion film, and have completed the present invention.
• D 1 is a group represented by formula (D-1) described below.
• Ar d11 is a group represented by any one of formulas (Ar-1) to (Ar-9) described below.
• Ar d11 is a group represented by the formula (Ar-10) described below.
• a photoelectric conversion element with excellent manufacturing suitability can be provided. Further, according to the present invention, an image sensor, an optical sensor, and a compound can be provided.
• FIG. 1 is a schematic cross-sectional view showing one configuration example of a photoelectric conversion element.
• FIG. 1 is a schematic cross-sectional view showing one configuration example of a photoelectric conversion element.
• a numerical range expressed using “ ⁇ ” means a range that includes the numerical values written before and after " ⁇ " as lower and upper limits.
• the hydrogen atom may be a light hydrogen atom (normal hydrogen atom) or a deuterium atom (eg, a double hydrogen atom).
• substituents, linking groups, etc. hereinafter also referred to as “substituents, etc." indicated by specific symbols, or when multiple substituents, etc. are specified at the same time, each This means that the substituents and the like may be the same or different. This point also applies to the definition of the number of substituents, etc.
• the "substituent” includes a group exemplified by the substituent W described below.
• the substituent W in this specification will be described.
• the substituent W is, for example, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.), an alkyl group (including a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group), an alkenyl group (cycloalkenyl and bicycloalkenyl groups), alkynyl groups, aryl groups, heteroaryl groups (heterocyclic groups), cyano groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclicoxy groups, acyloxy groups, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, secondary or tertiary amino group (including anilino group), alkylthio group, arylthio group, heterocycl
• each of the above-mentioned groups may further have a substituent (for example, one or more of the above-mentioned groups), if possible.
• a substituent for example, one or more of the above-mentioned groups
• an alkyl group which may have a substituent is also included as one form of the substituent W.
• the substituent W has a carbon atom
• the number of carbon atoms in the substituent W is, for example, 1 to 20.
• the number of atoms other than hydrogen atoms in the substituent W is, for example, 1 to 30.
• the specific compounds mentioned below include a carboxy group, a salt of a carboxy group, a salt of a phosphoric acid group, a sulfonic acid group, a salt of a sulfonic acid group, a hydroxy group, a thiol group, an acylamino group, a carbamoyl group, and a ureido group as substituents. , a boronic acid group (-B(OH) 2 ) and/or a primary amino group.
• examples of the substituent W include a group containing the group represented by A 1 and a 1,3-dicarbonyl ring group.
• examples of the 1,3-dicarbonyl ring group include a 1,3-indanedione ring group, a 1,3-cyclohexanedione ring group, a 5,5-dimethyl-1,3-cyclohexanedione ring group, and a 1,3-dicarbonyl ring group.
• a dioxane-4,6-dione ring group can be mentioned.
• examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• the alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 carbon atoms.
• the alkyl group may be linear, branched, or cyclic. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, t-butyl group, n-hexyl group and cyclopentyl group.
• the alkyl group may be any of a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group, and may have a cyclic structure of these as a partial structure.
• examples of the substituent that the alkyl group may have include the groups exemplified by the substituent W, and aryl groups (preferably 6 to 18 carbon atoms, more (preferably 6 carbon atoms), a heteroaryl group (preferably 5 to 18 carbon atoms, more preferably 5 to 6 carbon atoms), or a halogen atom (preferably a fluorine atom or a chlorine atom).
• the alkyl group moiety in the alkoxy group is preferably the above alkyl group.
• the alkyl group moiety in the alkylthio group is preferably the above alkyl group.
• examples of the substituent which the alkoxy group may have are similar to those of the alkyl group which may have a substituent.
• examples of the substituent which the alkylthio group may have are similar to the substituents in the alkyl group which may have a substituent.
• the alkenyl group may be linear, branched, or cyclic.
• the alkenyl group preferably has 2 to 20 carbon atoms.
• examples of the substituent which the alkenyl group may have are similar to the substituents in the alkyl group which may have a substituent.
• an alkynyl group may be linear, branched, or cyclic.
• the number of carbon atoms in the alkynyl group is preferably 2 to 20.
• examples of the substituent which the alkynyl group may have are similar to those of the alkyl group which may have a substituent.
• the aromatic ring or the aromatic ring constituting the aromatic ring group may be either monocyclic or polycyclic (eg, 2 to 6 rings, etc.) unless otherwise specified.
• a monocyclic aromatic ring is an aromatic ring having only one aromatic ring structure as a ring structure.
• a polycyclic (eg, 2-6 rings, etc.) aromatic ring is an aromatic ring in which a plurality of (eg, 2-6, etc.) aromatic ring structures are condensed as a ring structure.
• the number of ring member atoms in the aromatic ring is preferably 5 to 15.
• the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle.
• the number of heteroatoms it has as ring member atoms is, for example, 1 to 10.
• the heteroatoms include nitrogen atom, sulfur atom, oxygen atom, selenium atom, tellurium atom, phosphorus atom, silicon atom, and boron atom.
• the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring.
• aromatic heterocycle examples include a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, and a triazine ring (for example, a 1,2,3-triazine ring, a 1,2,4-triazine ring, and a 1,3,5-triazine ring).
• tetrazine ring e.g., 1,2,4,5-tetrazine ring, etc.
• quinoxaline ring pyrrole ring, furan ring, thiophene ring, imidazole ring, oxazole ring, thiazole ring, benzopyrrole ring, benzofuran ring, benzothiophene ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, naphtopyrrole ring, naphthofuran ring, naphthothiophene ring, naphthoimidazole ring, naphthoxazole ring, 3H-pyrrolidine ring, pyrroloimidazole ring (e.g., 5H- pyrrolo[1,2-a]imidazole ring, etc.), imidazoxazole ring (e.g., imidazo[
• the aromatic ring which may have a substituent examples of the types of substituents that the aromatic ring may have include the groups exemplified by the substituent W.
• the number of substituents may be 1 or more (eg, 1 to 4, etc.).
• the aromatic ring group includes, for example, a group obtained by removing one or more (eg, 1 to 5, etc.) hydrogen atoms from the above aromatic ring.
• the term aryl group includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic hydrocarbon ring among the above aromatic rings.
• heteroaryl group includes, for example, a group obtained by removing one hydrogen atom from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings.
• the arylene group includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic hydrocarbon ring among the above aromatic rings.
• the term “heteroarylene group” includes, for example, a group obtained by removing two hydrogen atoms from a ring corresponding to an aromatic heterocycle among the above-mentioned aromatic rings.
• examples of the types of substituents that these groups may have include the groups exemplified by the substituent W.
• the number of substituents may be 1 or more (eg, 1 to 4, etc.).
• the bonding direction of the divalent groups (eg, -CO-O-, etc.) described herein is not limited unless otherwise specified.
• Y in a compound represented by the formula "X-Y-Z" is -CO-O-
• the above compound has the formula "X-O-CO-Z" and "X-CO-O- Z" may be used.
• the photoelectric conversion element of the present invention includes a first embodiment and a second embodiment.
• the photoelectric conversion element of the first embodiment is a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, and the photoelectric conversion film is a compound represented by formula (1) (hereinafter referred to as , also referred to as "Specific Compound 1").
• the photoelectric conversion element of the second embodiment is a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, and the photoelectric conversion film is a compound represented by formula (2) (hereinafter referred to as , also referred to as "specific compound 2").
• the specific compound 1 and the specific compound 2 will be collectively referred to as the specific compound.
• a feature of the present invention is that it contains a specific compound, and it is presumed that the characteristic chemical structure of the specific compound provides excellent suitability for producing a photoelectric conversion film containing the specific compound.
• specific compound 1 has a structure A 1 containing a nitrogen atom at a specific position
• specific compound 2 has a structure A 2 containing a nitrogen atom at a specific position and a specific structure D 2 . It is thought that the above effects can be achieved depending on the point.
• “more excellent manufacturing suitability” is also referred to as “more excellent effects of the present invention.”
• FIG. 1 shows a schematic cross-sectional view of an embodiment of the photoelectric conversion element of the present invention.
• the photoelectric conversion element 10a shown in FIG. 1 includes a conductive film 11 functioning as a lower electrode (hereinafter also referred to as "lower electrode”), an electron blocking film 16A, a photoelectric conversion film 12 containing a specific compound, and an upper electrode. It has a structure in which a transparent conductive film (hereinafter also referred to as "upper electrode”) 15 that functions as an upper electrode is laminated in this order.
• FIG. 2 shows a configuration example of another photoelectric conversion element.
• FIGS. 1 and 2 has a structure in which an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15 are laminated in this order on a lower electrode 11. Note that the stacking order of the electron blocking film 16A, the photoelectric conversion film 12, and the hole blocking film 16B in FIGS. 1 and 2 may be changed as appropriate depending on the application and characteristics.
• the photoelectric conversion element 10a it is preferable that light be incident on the photoelectric conversion film 12 via the upper electrode 15. Further, when using the photoelectric conversion element 10a (or 10b), a voltage can be applied. In this case, it is preferable that the lower electrode 11 and the upper electrode 15 form a pair of electrodes, and a voltage of 1 ⁇ 10 ⁇ 5 to 1 ⁇ 10 7 V/cm is applied between the pair of electrodes. In terms of performance and power consumption, the applied voltage is more preferably 1 ⁇ 10 ⁇ 4 to 1 ⁇ 10 7 V/cm, and even more preferably 1 ⁇ 10 ⁇ 3 to 5 ⁇ 10 6 V/cm. Regarding the voltage application method, in FIGS.
• the photoelectric conversion element 10a (or 10b) is used as a photosensor or incorporated into an image sensor, voltage can be applied in a similar manner. As will be described in detail later, the photoelectric conversion element 10a (or 10b) can be suitably applied to an image sensor.
• the specific compound includes any of the geometric isomers.
• both the cis form and the trans form, which are distinguished based on the C ⁇ C double bond, are included in the specific compound.
• the photoelectric conversion element of the first embodiment is a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, and the photoelectric conversion film contains the specific compound 1.
• the photoelectric conversion element of the first embodiment has a photoelectric conversion film.
• the photoelectric conversion film contains specific compound 1.
• D 1 A 1 (1)
• a 1 represents a group represented by any one of formulas (A-1) to (A-3).
• D 1 represents a divalent organic group.
• * represents the bonding position.
• R W11 represents a hydrogen atom or a substituent.
• R Z11 to R Z13 each independently represent a hydrogen atom or a substituent.
• * represents the bonding position.
• R W21 represents a hydrogen atom or a substituent.
• R Z21 to R Z23 each independently represent a hydrogen atom or a substituent.
• * represents the bonding position.
• R W31 is a hydrogen atom, a halogen atom, a cyano group, an aromatic ring group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, -OR W32 , -SR W33 , - Represents Si(R W34 ) 3 , -N(R W35 ) 2 or a group having a phosphorus atom.
• R W32 and R W33 each independently represent a substituent.
• R W34 and R W35 each independently represent a hydrogen atom or a substituent.
• R Z31 to R Z33 each independently represent a hydrogen atom or a substituent.
• R W11 a hydrogen atom is preferable. When a plurality of R W11s exist, the R W11s may be the same or different.
• R Z11 to R Z13 each independently represent a hydrogen atom or a substituent.
• Z 11 and Z 12 an oxygen atom or a sulfur atom is preferable, and an oxygen atom is more preferable.
• the substituents represented by R Z11 to R Z13 include the groups exemplified by substituent W.
• the R Z11 's may be the same or different.
• the R Z12s may be the same or different.
• the R Z13s may be the same or different.
• R Z21 to R Z23 each independently represent a hydrogen atom or a substituent.
• Z 21 and Z 22 an oxygen atom or a sulfur atom is preferable, and an oxygen atom is more preferable.
• R Z21 to R Z23 include groups represented by R Z11 to R Z13 , respectively.
• the R Z21 's may be the same or different.
• the R Z22s may be the same or different.
• the R Z23s may be the same or different.
• R W31 is a hydrogen atom, a halogen atom, a cyano group, an aromatic ring group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, -OR W32 , -SR W33 , - Represents Si(R W34 ) 3 , -N(R W35 ) 2 or a group having a phosphorus atom.
• R W32 and R W33 each independently represent a substituent.
• R W34 and R W35 each independently represent a hydrogen atom or a substituent.
• the aromatic ring group may be either an aryl group that may have a substituent or a heteroaryl group that may have a substituent.
• the aliphatic hydrocarbon group may be linear, branched, or cyclic, and may be saturated or unsaturated. Examples of the aliphatic hydrocarbon group include an alkyl group, an alkenyl group, and an alkynyl group that may have a substituent. Examples of the substituents that the aromatic ring group and the aliphatic hydrocarbon group may have include the groups exemplified by the substituent W.
• R W32 to R W35 examples include the groups exemplified by substituent W.
• R W31 a hydrogen atom is preferable.
• the R W31s may be the same or different.
• R Z31 to R Z33 each independently represent a hydrogen atom or a substituent.
• Z 31 is preferably an oxygen atom or a sulfur atom, more preferably an oxygen atom.
• R Z31 to R Z33 include groups represented by R Z11 to R Z13 , respectively. When a plurality of R Z31 's exist, the R Z31 's may be the same or different. When a plurality of R Z32 's exist, the R Z32 's may be the same or different. When a plurality of R Z33s exist, the R Z33s may be the same or different.
• Z 11 , Z 12 , Z 21 , Z 22 and Z 31 are preferably oxygen atoms or sulfur atoms.
• D 1 represents a divalent organic group.
• the divalent organic group is not particularly limited as long as it satisfies the above conditions.
• D 1 may contain a group represented by any of the above formulas (A-1) to (A-3) as a partial structure.
• D 1 is preferably a group represented by formula (D-1).
• Ar d11 represents a substituent having an aromatic ring.
• R d11 to R d13 each independently represent a hydrogen atom or a substituent.
• n d11 represents an integer from 0 to 5.
• R d11 to R d13 each independently represent a hydrogen atom or a substituent.
• substituents represented by R d11 to R d13 include the groups exemplified by substituent W.
• R d11 to R d13 are preferably hydrogen atoms.
• the R d12s may be the same or different.
• the R d13s may be the same or different.
• n d11 represents an integer of 0 to 5.
• nd11 is preferably 0 or 1, and more preferably 0.
• Ar d11 represents a substituent having an aromatic ring.
• a substituent having an aromatic ring is a group having an aromatic ring in part or all of the substituent.
• the substituent having an aromatic ring may include a group represented by any of the above-mentioned formulas (A-1) to (A-3) as a partial structure.
• Ar d11 an aryl group which may have a substituent or a heteroaryl group which may have a substituent is preferable. It is also preferable that Ar d11 is a substituent having a condensed polycyclic aromatic heterocycle. Examples of the substituent that the aryl group and the heteroaryl group may have include the groups exemplified by the substituent W.
• Ar d11 may be monocyclic or polycyclic.
• the above polycyclic ring may be a fused ring.
• the total number of aromatic rings possessed by Ar d11 is preferably from 5 to 40, more preferably from 10 to 30, even more preferably from 20 to 30.
• the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a combination thereof.
• aromatic heterocycle examples include a thiophene ring, a furan ring, a pyran ring, a thiazole ring, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an oxazole ring, a selenophene ring, an imidazole ring, a quinoxaline ring, and a benzothiazole ring.
• Ar d11 may further have other rings in addition to the above-mentioned aromatic ring.
• Other rings may be fused with the above aromatic ring to form a fused ring.
• the other rings include a cycloalkane ring, a piperidine ring, a piperazine ring, an imidazolidine ring, and a combination thereof.
• Ar d11 is preferably a group represented by any one of formulas (Ar-1) to (Ar-9), including formulas (Ar-1) to (Ar-3), formulas (Ar-8) and A group represented by formula (Ar-9) is more preferred, a group represented by formula (Ar-1) is even more preferred, a group represented by formula (Ar-10) is particularly preferred, and a group represented by formula (Ar-1) is particularly preferred; The group represented by Ar-11) is most preferred.
• R 11 to R 13 each independently represent a hydrogen atom or a substituent. At least two of R 11 to R 13 may be bonded to each other to form a ring.
• T 11 and T 12 each independently represent an oxygen atom, a sulfur atom, a selenium atom, -NR 14 - or -C(R 15 )(R 16 )-.
• R 14 to R 16 each independently represent a hydrogen atom, an alkyl group that may have a substituent, or an aromatic ring group that may have a substituent.
• * represents the bonding position.
• Ar 21 represents an aromatic ring containing two or more carbon atoms and optionally having a substituent.
• R 21 and R 22 each independently represent a hydrogen atom or a substituent.
• R 21 and R 22 may be bonded to each other to form a ring.
• R 23 to R 27 each independently represent a hydrogen atom or a substituent.
• R 23 and R 24 or R 25 and R 26 may be bonded to each other to form a ring.
• R 29 and R 30 each independently represent a hydrogen atom or a substituent. At least one of R 29 and R 30 and at least one of Ar 21 , R 21 and R 22 may be bonded to each other to form a ring.
• * represents the bonding position.
• R 31 represents a hydrogen atom or a substituent.
• * represents the bonding position.
• X 41 represents an oxygen atom, a sulfur atom, a selenium atom or -NR 42 -.
• R 41 and R 42 each independently represent a hydrogen atom or a substituent.
• R 43 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
• * represents the bonding position.
• R 51 represents a hydrogen atom or a substituent.
• X 61 represents an oxygen atom, a sulfur atom, a selenium atom or -NR 62 -.
• R 61 and R 62 each independently represent a hydrogen atom or a substituent.
• X 71 represents an oxygen atom, a sulfur atom, a selenium atom or -NR 72 -.
• R 71 and R 72 each independently represent a hydrogen atom or a substituent.
• X 81 and X 82 each independently represent an oxygen atom, a sulfur atom, a selenium atom or -NR 82 -.
• R 81 and R 82 each independently represent a hydrogen atom or a substituent.
• R 83 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group.
• * represents the bonding position.
• X 91 to X 93 each independently represent an oxygen atom, a sulfur atom, a selenium atom, or -NR 92 -.
• R 91 and R 92 each independently represent a hydrogen atom or a substituent.
• R 93 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group.
• R 11 to R 13 each independently represent a hydrogen atom or a substituent. At least two of R 11 to R 13 may be bonded to each other to form a ring.
• the substituent represented by R 11 include the groups exemplified by substituent W.
• R 11 is preferably a hydrogen atom.
• R 12 and R 13 include groups exemplified by substituent W, such as an alkyl group that may have a substituent or an aromatic ring group that may have a substituent (preferably, An aryl group which may have a substituent is preferred.
• a 1 has the same meaning as A 1 in formula (1).
• R 12 and R 13 are preferably bonded to each other to form a ring.
• the ring formed above is preferably an aromatic heterocycle, and more preferably a quinoxaline ring or a pyrazine ring.
• an aromatic hydrocarbon ring is also preferable, and a benzene ring is more preferable.
• the ring formed above may further have a substituent. Examples of the above-mentioned substituent include groups exemplified by the substituent W, preferably an alkyl group that may have a substituent, a chlorine atom, a fluorine atom, or a cyano group, and an alkyl group or a chlorine atom is more preferable. preferable.
• T 11 and T 12 each independently represent an oxygen atom, a sulfur atom, a selenium atom, -NR 14 - or -C(R 15 )(R 16 )-.
• R 14 to R 16 each independently represent a hydrogen atom, an alkyl group that may have a substituent, or an aromatic ring group that may have a substituent.
• T 11 and T 12 -NR 14 - or -C(R 15 )(R 16 )- is preferable.
• R 15 and R 16 may be bonded to each other to form a ring.
• the ring formed above is preferably a cycloalkane ring, more preferably a cyclohexane ring.
• the alkyl group may be linear, branched, or cyclic.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 3.
• the aromatic ring group may be either an aryl group that may have a substituent or a heteroaryl group that may have a substituent, and the aryl group that may have a substituent may be an aryl group that may have a substituent. preferable.
• the aromatic ring group may be either monocyclic or polycyclic.
• the above polycyclic ring may be a fused ring.
• the number of carbon atoms in the aromatic ring group is preferably 3 to 30, more preferably 3 to 15.
• the number of substituents that the aromatic ring group has is preferably 1 to 5, more preferably 2 or 3.
• Examples of the substituents that the alkyl group and the aromatic ring group may have include the groups exemplified by the substituent W.
• the substituent that the aromatic ring group may have is preferably an alkyl group or a heteroaryl group, and more preferably an alkyl group having 1 to 3 carbon atoms.
• the above aromatic ring group is preferably a phenyl group, a naphthyl group or a fluorenyl group which may have a substituent, more preferably a phenyl group which may have a substituent, and further a phenyl group which may have a substituent. preferable. It is also preferable that T 11 and T 12 represent the same group.
• R 14s may be the same or different.
• R 15s may be the same or different.
• R 16s may be the same or different.
• R 14 to R 16 may be a group represented by formula (R-1).
• R 14 is preferably a group represented by formula (R-1).
• R 15 and R 16 are preferably an alkyl group that may have a substituent, and more preferably an unsubstituted alkyl group.
• R r1 and R r2 each independently represent an alkyl group that may have a substituent or an aromatic ring group that may have a substituent.
• R r3 represents a hydrogen atom or a substituent.
• R r1 and R r2 each independently represent an alkyl group that may have a substituent or an aromatic ring group that may have a substituent.
• the alkyl group and the aromatic ring group include the alkyl group which may have a substituent and the aromatic ring group which may have a substituent represented by R 14 to R 16 .
• R r1 and R r2 are preferably an alkyl group that may have a substituent or an aryl group that may have a substituent.
• R r3 represents a hydrogen atom or a substituent.
• substituent W examples of the above-mentioned substituent include groups exemplified by substituent W.
• R r3 is preferably a hydrogen atom or an alkyl group. When a plurality of R r3s exist, R r3s may be the same or different.
• Ar 21 represents an aromatic ring containing two or more carbon atoms and optionally having a substituent.
• "Two or more carbon atoms” means that the aromatic ring represented by Ar 21 includes two carbon atoms forming a bond between the aromatic ring represented by Ar 21 and the ring containing T 21 and T 22 . , means that it may further contain carbon atoms in addition to the above two carbon atoms. In other words, the aromatic ring represented by Ar 21 contains the above two carbon atoms as ring member atoms.
• the aromatic ring may be either monocyclic or polycyclic.
• the above polycyclic ring may be a fused ring.
• the number of ring members in the aromatic ring is preferably 3 to 12, more preferably 3 to 6.
• the number of carbon atoms in the aromatic ring is 2 or more, preferably 3 to 20, more preferably 5 to 12.
• the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle.
• Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a combination thereof.
• Examples of the aromatic heterocycle include a thiophene ring, a furan ring, a pyran ring, a thiazole ring, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an oxazole ring, a selenophene ring, an imidazole ring, a quinoxaline ring, and a benzothiazole ring.
• Examples include rings and rings that are a combination thereof.
• the aromatic ring is more preferably a benzene ring, a naphthalene ring or a thiophene ring.
• Examples of the substituent that the aromatic ring may have include the groups exemplified by the substituent W.
• R 21 and R 22 each independently represent a hydrogen atom or a substituent.
• R 21 and R 22 may be bonded to each other to form a ring.
• substituents represented by R 21 and R 22 include substituents represented by R 12 and R 13 .
• the ring formed by combining R 21 and R 22 with each other include a ring formed by combining R 12 and R 13 with each other, preferably an aromatic hydrocarbon ring, and more preferably a benzene ring. .
• R 23 to R 27 each independently represent a hydrogen atom or a substituent.
• R 23 and R 24 or R 25 and R 26 may be bonded to each other to form a ring.
• R 29 and R 30 each independently represent a hydrogen atom or a substituent.
• At least one of R 29 and R 30 and at least one of Ar 21 , R 21 and R 22 may be bonded to each other to form a ring.
• T 21 and T 22 -C(R 23 )(R 24 )- or -NR 27 - is preferable.
• the substituents represented by R 23 to R 27 include the groups exemplified by the substituent W, with an alkyl group being preferred, and an alkyl group having 1 to 3 carbon atoms being more preferred.
• an aromatic ring group is also preferable, and a benzene ring group is more preferable.
• the substituents represented by R 29 and R 30 include the groups exemplified by substituent W.
• At least one of R 29 and R 30 and at least one of Ar 21 , R 21 and R 22 may be bonded to each other to form a ring. When there are multiple identical notations, the same notations may be the same or different.
• R 31 represents a hydrogen atom or a substituent.
• substituent represented by R 31 include a diarylamino group, the substituents represented by R 12 and R 13 , and an aryl group that may have a substituent or an aryl group that may have a substituent.
• An optional heteroaryl group is preferred.
• substituent that the aryl group and the heteroaryl group may have a -aromatic heterocycle-aromatic hydrocarbon ring-1,3-dicarbonyl ring group is preferred.
• R 32 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
• R 32 may be bonded to each other to form a ring.
• R 32 a hydrogen atom is preferable.
• the R 32s may be the same or different.
• X 41 represents an oxygen atom, a sulfur atom, a selenium atom or -NR 42 -.
• X 41 an oxygen atom or a sulfur atom is preferable, and a sulfur atom is more preferable.
• R 41 and R 42 each independently represent a hydrogen atom or a substituent.
• substituent represented by R 41 and R 42 include the substituents represented by R 12 and R 13 , and an aryl group that may have a substituent or an aryl group that has a substituent.
• a heteroaryl group is preferred.
• the R 42s may be the same or different.
• R 43 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
• R 43 may be bonded to each other to form a ring.
• R43 a hydrogen atom is preferable.
• R 43s may be the same or different.
• R 51 represents a hydrogen atom or a substituent.
• substituents represented by R 51 include substituents represented by R 12 and R 13 .
• R 52 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
• R 52 may be bonded to each other to form a ring.
• R52 a hydrogen atom is preferable.
• the R 52s may be the same or different.
• X 61 represents an oxygen atom, a sulfur atom, a selenium atom or -NR 62 -.
• X 61 an oxygen atom or a sulfur atom is preferable.
• R 61 and R 62 each independently represent a hydrogen atom or a substituent.
• substituents represented by R 61 and R 62 include substituents represented by R 12 and R 13 .
• the R 62s may be the same or different.
• R 63 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
• R 63 may be bonded to each other to form a ring.
• R 63 is preferably a hydrogen atom. When a plurality of R 63s exist, the R 63s may be the same or different.
• X 71 represents an oxygen atom, a sulfur atom, a selenium atom or -NR 72 -.
• X 71 is preferably an oxygen atom or a sulfur atom.
• R 71 and R 72 each independently represent a hydrogen atom or a substituent.
• substituents represented by R 71 and R 72 include substituents represented by R 12 and R 13 .
• the R 72s may be the same or different.
• R 73 represents a hydrogen atom, a halogen atom, a trifluoromethyl group or a cyano group.
• R 73 is preferably a hydrogen atom. When a plurality of R 73s exist, the R 73s may be the same or different.
• X 81 and X 82 each independently represent an oxygen atom, a sulfur atom, a selenium atom or -NR 81 -. It is preferable that one of X 81 and X 82 represents an oxygen atom or a sulfur atom, and the other represents -NR 81 -. When a plurality of R 82s exist, the R 82s may be the same or different.
• R 81 and R 82 represent a hydrogen atom or a substituent.
• substituent represented by R 81 and R 82 include the substituents represented by R 12 and R 13 , and an alkyl group that may have a substituent or an alkyl group that has a substituent.
• Aromatic ring groups are preferred.
• R 83 represents a hydrogen atom, a halogen atom, a trifluoromethyl group, or a cyano group.
• R 83 is preferably a hydrogen atom. When a plurality of R 83s exist, the R 83s may be the same or different.
• X 91 to X 93 each independently represent an oxygen atom, a sulfur atom, a selenium atom, or -NR 92 -. At least one of X 91 to X 93 preferably represents an oxygen atom or a sulfur atom, and more preferably at least two of X 91 to X 93 represent a sulfur atom.
• R 91 and R 92 each independently represent a hydrogen atom or a substituent.
• substituents represented by R 91 and R 92 include the substituents represented by R 12 and R 13 , and an alkyl group that may have a substituent or an alkyl group that has a substituent.
• Aromatic ring groups are preferred.
• Examples of the 1,3-dicarbonyl ring group include a 1,3-indanedione ring group, a 1,3-cyclohexanedione ring group, a 5,5-dimethyl-1,3-cyclohexanedione ring group, and a 1,3-dicarbonyl ring group.
• a dioxane-4,6-dione ring group may be mentioned.
• the R 92s may be the same or different.
• R 93 is preferably a hydrogen atom. When a plurality of R 93s exist, the R 93s may be the same or different.
• R 101 represents a hydrogen atom or a substituent.
• R 102 and R 103 each independently represent a hydrogen atom, an alkyl group that may have a substituent, or an aromatic ring group that may have a substituent.
• Ar 101 represents an aromatic ring containing two or more carbon atoms and optionally having a substituent.
• R 101 represents a hydrogen atom or a substituent.
• substituent represented by R 101 include the substituent represented by R 11 .
• R 101 a hydrogen atom is preferable.
• R 102 and R 103 each independently represent a hydrogen atom, an alkyl group that may have a substituent, or an aromatic ring group that may have a substituent.
• R 102 and R 103 include the group represented by R 14 .
• Ar 101 represents an aromatic ring containing two or more carbon atoms and optionally having a substituent.
• "Two or more carbon atoms” means two or more carbon atoms in which the aromatic ring represented by Ar 101 forms a bond between the aromatic ring represented by Ar 101 and the ring containing -NR 102 - and -NR 103 -. It means that it contains a carbon atom and may further contain a carbon atom in addition to the above two carbon atoms. In other words, the aromatic ring represented by Ar 101 contains the above two carbon atoms as ring member atoms.
• the aromatic ring may be either monocyclic or polycyclic.
• the above polycyclic ring may be a fused ring.
• the number of ring members in the aromatic ring is preferably 3 to 12.
• the number of carbon atoms in the aromatic ring is 2 or more, preferably 3 to 20, more preferably 5 to 12.
• the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a combination thereof.
• aromatic heterocycle examples include a thiophene ring, a furan ring, a pyran ring, a thiazole ring, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an oxazole ring, a selenophene ring, an imidazole ring, a quinoxaline ring, and a benzothiazole ring.
• the aromatic ring is preferably an aromatic heterocycle, and more preferably a quinoxaline ring or a pyrazine ring.
• substituent W examples include the groups exemplified by substituent W, such as an alkyl group that may have a substituent, a chlorine atom, a fluorine atom, or a cyano atom. Groups are preferred.
• R 111 represents a hydrogen atom or a substituent.
• R 112 and R 113 each independently represent a hydrogen atom, an alkyl group that may have a substituent, or an aromatic ring group that may have a substituent.
• R 114 and R 115 each independently represent a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent.
• R 116 represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
• R 111 represents a hydrogen atom or a substituent.
• Examples of the substituent represented by R 111 include the substituent represented by R 11 .
• R 112 and R 113 each independently represent a hydrogen atom, an alkyl group that may have a substituent, or an aromatic ring group that may have a substituent.
• R 112 and R 113 include the group represented by R 14 .
• R 114 and R 115 each independently represent a hydrogen atom, a halogen atom, or an alkyl group which may have a substituent.
• the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom or a chlorine atom being preferred.
• the alkyl group may be linear, branched, or cyclic.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 3, and even more preferably 1.
• the substituents that the alkyl group may have include the groups exemplified by the substituent W.
• R 114 and R 115 an alkyl group which may have a substituent is preferable, and an alkyl group without a substituent (unsubstituted alkyl group) is more preferable.
• R 116 represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
• -CR 116 is preferable.
• the alkyl group which may have a substituent and the aromatic ring group which may have a substituent represented by R 116 include, for example, those having a substituent represented by R 14 to R 16 .
• Examples include an optionally substituted alkyl group and an optionally substituted aromatic ring group.
• R 116 a hydrogen atom is preferable. When a plurality of R 116s exist, R 116s may be the same or different.
• D 1 is a group represented by the formula (D-1), in the formula (D-1), n d11 is 0, and Ar d11 is the group represented by the formula (Ar-1).
• a 1 is a group represented by formula (A-1)
• the compound represented by formula (1) becomes a compound represented by formula (X-1).
• D 1 is a group represented by formula (D-1), in formula (D-1), n d11 is 1, and Ar d11 is a group represented by formula (Ar-3).
• a 1 is represented by formula (A-2), it becomes a compound represented by formula (X-2).
• Examples of the specific compound 1 include the following compounds.
• Compounds 1-1 to 1-7 are compounds in which Ar d11 is a group represented by formula (Ar-1), and compound 1-8 is a compound in which Ar d11 is a group represented by formula (Ar-3).
• Compounds 1-9 and 1-10 are compounds in which Ar d11 is a group represented by formula (Ar-2), and compounds 1-11 and 1-12 are compounds in which Ar is a group represented by formula (Ar-2).
• a compound in which d11 is a group represented by formula (Ar-8), and compounds 1-13 and 1-14 are compounds in which Ar d11 is a group represented by formula (Ar-9), Compound 1-15 is a compound in which Ar d11 is a group represented by formula (Ar-4), and compound 1-16 is a compound in which Ar d11 is a group represented by formula (Ar-3). be.
• the molecular weight of the specific compound 1 is preferably 400 to 1,200, more preferably 400 to 1,000, even more preferably 400 to 800.
• the sublimation temperature of the specific compound 1 becomes low, and it is presumed that the photoelectric conversion efficiency is excellent even when a photoelectric conversion film is formed at high speed.
• Specific Compound 1 is particularly useful as a material for a photoelectric conversion film used in an image sensor, a photosensor, or a photovoltaic cell.
• the specific compound 1 often functions as a dye within the photoelectric conversion film.
• the specific compound 1 can be used as a coloring material, a liquid crystal material, an organic semiconductor material, a charge transport material, a pharmaceutical material, and a fluorescent diagnostic material.
• Specific Compound 1 has an ionization potential of -5.0 to -6.0 eV in a single film in terms of stability when used as a p-type organic semiconductor and energy level matching with an n-type organic semiconductor. It is preferable.
• the maximum absorption wavelength of the specific compound 1 is preferably in the range of 400 to 600 nm, more preferably in the range of 450 to 580 nm.
• the above maximum absorption wavelength is a value measured in a solution state (solvent: chloroform) by adjusting the absorption spectrum of Specific Compound 1 to a concentration such that the absorbance is 0.5 to 1.0.
• solvent chloroform
• the maximum absorption wavelength of the specific compound 1 is determined by vapor-depositing the specific compound 1 and using the specific compound 1 in a film state.
• Specific Compound 1 may be purified if necessary.
• purification methods for specific compound 1 include sublimation purification, purification using silica gel column chromatography, purification using gel permeation chromatography, reslurry washing, reprecipitation purification, purification using an adsorbent such as activated carbon, and repurification. Examples include crystal purification.
• Specific Compound 1 may be used alone or in combination of two or more.
• the photoelectric conversion film contains an n-type organic semiconductor in addition to the specific compound 1 described above.
• the n-type organic semiconductor is a compound different from the specific compound 1 above.
• An n-type organic semiconductor is an acceptor organic semiconductor material (compound), and refers to an organic compound that has the property of easily accepting electrons. That is, an n-type organic semiconductor refers to an organic compound that has a larger electron affinity when two organic compounds are used in contact with each other. That is, any organic compound can be used as the acceptor organic semiconductor as long as it has electron-accepting properties.
• n-type organic semiconductors include fullerenes selected from the group consisting of fullerenes and derivatives thereof; fused aromatic carbocyclic compounds (for example, naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pyrene derivatives, perylene derivatives, fluoranthene derivatives, etc.); 5- to 7-membered heterocyclic compounds having at least one member selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms (e.g., pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, quinoxaline); , quinazoline, phthalazine, cinnoline, isoquinoline, pteridine, acridine, phenazine, phenanthroline, tetrazole, pyrazole, imidazole and thiazole, etc.
• fullerenes selected from the group consisting of fullerenes and derivatives thereof are preferred.
• fullerenes include fullerene C 60 , fullerene C 70 , fullerene C 76 , fullerene C 78 , fullerene C 80 , fullerene C 82 , fullerene C 84 , fullerene C 90 , fullerene C 96 , fullerene C 240 , fullerene C 540 , and Mixed fullerenes are mentioned.
• fullerene derivatives include compounds obtained by adding a substituent to the above fullerene.
• the above substituent is preferably an alkyl group, an aryl group or a heterocyclic group.
• the fullerene derivative compounds described in JP-A No. 2007-123707 are preferred.
• the n-type organic semiconductor may be an organic dye.
• organic dyes include cyanine dyes, styryl dyes, hemicyanine dyes, merocyanine dyes (including zeromethine merocyanine (simple merocyanine)), rhodacyanine dyes, allopolar dyes, oxonol dyes, hemioxonol dyes, squalium dyes, croconium dyes, azamethine dyes, coumarin dyes, arylidene dyes, anthraquinone dyes, triphenylmethane dyes, azo dyes, azomethine dyes, metallocene dyes, fluorenone dyes, fulgide dyes, perylene dyes, phenazine dyes, phenothiazine dyes, quinone dyes, diphenylmethane dyes, polyene dyes, Examples include acridine dyes,
• the molecular weight of the n-type organic semiconductor is preferably 200 to 1,200, more preferably 200 to 900.
• the maximum absorption wavelength of the n-type organic semiconductor is preferably a wavelength of 400 nm or less or a wavelength range of 500 to 600 nm.
• the photoelectric conversion film has a bulk heterostructure formed in a state in which the specific compound 1 and an n-type organic semiconductor are mixed.
• the bulk heterostructure is a layer in which the specific compound 1 and the n-type organic semiconductor are mixed and dispersed within the photoelectric conversion film.
• a photoelectric conversion film having a bulk heterostructure can be formed by either a wet method or a dry method. Note that the bulk heterostructure is explained in detail in paragraphs [0013] to [0014] of JP-A No. 2005-303266.
• the difference in electron affinity between the specific compound 1 and the n-type organic semiconductor is preferably 0.1 eV or more.
• the n-type organic semiconductors may be used alone or in combination of two or more.
• the content of the n-type organic semiconductor in the photoelectric conversion film is 15 It is preferably 75% by volume, more preferably 20-60% by volume, even more preferably 20-50% by volume.
• the content of fullerenes relative to the total content of the n-type organic semiconductor material is preferably 50 to 100% by volume, more preferably 80 to 100% by volume.
• Fullerenes may be used alone or in combination of two or more.
• the content of specific compound 1 relative to the total content of specific compound 1 and n-type organic semiconductor (film thickness in terms of a single layer of specific compound 1/(single layer of specific compound 1)
• the value (film thickness in terms of conversion + film thickness in terms of single layer of n-type organic semiconductor) x 100) is preferably 20 to 80% by volume, more preferably 40 to 80% by volume.
• the content of specific compound 1 (film thickness in terms of a single layer of specific compound 1 / (film thickness in terms of a single layer of specific compound 1 + n-type
• the thickness of the organic semiconductor in terms of a single layer+the thickness of the p-type organic semiconductor in terms of a single layer) ⁇ 100) is preferably 15 to 75% by volume, more preferably 30 to 75% by volume.
• the photoelectric conversion film is substantially composed of the specific compound 1, an n-type organic semiconductor, and a p-type organic semiconductor included as desired.
• Substantially means that the total content of the specific compound 1, the n-type organic semiconductor and the p-type organic semiconductor is 90 to 100% by volume, preferably 95 to 100% by volume, with respect to the total mass of the photoelectric conversion film. More preferably 99 to 100% by volume.
• the photoelectric conversion film contains a p-type organic semiconductor in addition to the specific compound 1 described above.
• the p-type organic semiconductor is a compound different from the above-mentioned specific compound 1.
• a p-type organic semiconductor is a donor organic semiconductor material (compound), and refers to an organic compound that has the property of easily donating electrons. That is, a p-type organic semiconductor refers to an organic compound that has a smaller ionization potential when two organic compounds are used in contact with each other.
• the p-type organic semiconductors may be used alone or in combination of two or more.
• Examples of p-type organic semiconductors include triarylamine compounds (for example, N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4, 4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl ( ⁇ -NPD), compound described in paragraphs [0128] to [0148] of JP 2011-228614, JP 2011-176259 Compounds described in paragraphs [0052] to [0063] of Japanese Patent Publication No. 2011-225544, compounds described in paragraphs [0119] to [0158] of Japanese Patent Application Publication No.
• TPD N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine
• ⁇ -NPD 4, 4'-bis[N-(naphthyl)-N-phenyl-amino]biphenyl
• naphthalene derivatives anthracene derivatives, phenanthrene derivatives, tetracene derivatives, pentacene derivatives, pyrene derivatives, perylene derivatives and fluoranthene derivatives, etc.
• porphyrin compounds phthalocyanine compounds
• triazole compounds oxa Examples include diazole compounds, imidazole compounds, polyarylalkane compounds, pyrazolone compounds, amino-substituted chalcone compounds, oxazole compounds, fluorenone compounds, silazane compounds, and metal complexes having nitrogen-containing heterocyclic compounds as ligands.
• Examples of the p-type organic semiconductor include compounds having a smaller ionization potential than the n-type organic semiconductor, and if this condition is satisfied, the organic dyes exemplified as the n-type organic semiconductor can be used. Examples of compounds that can be used as p-type organic semiconductor compounds are listed below.
• the difference in ionization potential between the specific compound 1 and the p-type organic semiconductor is preferably 0.1 eV or more.
• the p-type semiconductor materials may be used alone or in combination of two or more.
• the content of the p-type organic semiconductor in the photoelectric conversion film is 15 It is preferably 75% by volume, more preferably 20-60% by volume, even more preferably 25-50% by volume.
• the photoelectric conversion film containing the specific compound 1 is a non-luminescent film and has different characteristics from organic light emitting diodes (OLEDs).
• a non-luminescent film means a film with a luminescence quantum efficiency of 1% or less, preferably 0.5% or less, more preferably 0.1% or less. The lower limit is often 0% or more.
• Dry film forming methods include, for example, physical vapor deposition methods such as evaporation methods (especially vacuum evaporation methods), sputtering methods, ion plating methods, and MBE (Molecular Beam Epitaxy) methods, as well as CVD (Chemical) methods such as plasma polymerization. Vapor Deposition) method is mentioned, and vacuum evaporation method is preferable.
• manufacturing conditions such as the degree of vacuum and the evaporation temperature can be set according to a conventional method.
• the thickness of the photoelectric conversion film is preferably 10 to 1000 nm, more preferably 50 to 800 nm, and even more preferably 50 to 500 nm.
• the photoelectric conversion element has an electrode.
• the electrodes (upper electrode (transparent conductive film) 15 and lower electrode (conductive film) 11) are made of a conductive material. Electrically conductive materials include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Since light is incident from the upper electrode 15, it is preferable that the upper electrode 15 is transparent to the light to be detected. Examples of the material constituting the upper electrode 15 include antimony tin oxide (ATO), fluorine doped tin oxide (FTO), tin oxide, zinc oxide, indium oxide, and indium tin oxide (ITO).
• ATO antimony tin oxide
• FTO fluorine doped tin oxide
• ITO indium tin oxide
• Conductive metal oxides such as Indium Tin Oxide (Indium Tin Oxide) and Indium Zinc Oxide (IZO); Metal thin films such as gold, silver, chromium, and nickel; Mixtures or laminations of these metals and conductive metal oxides. and organic conductive materials such as polyaniline, polythiophene, and polypyrrole, nanocarbon materials such as carbon nanotubes and graphene, and conductive metal oxides are preferred in terms of high conductivity and transparency.
• the sheet resistance may be 100 to 10,000 ⁇ / ⁇ , and there is a large degree of freedom in the range of film thickness that can be made thin.
• An increase in light transmittance is preferable because it increases light absorption in the photoelectric conversion film and increases photoelectric conversion ability.
• the thickness of the upper electrode 15 is preferably 5 to 100 nm, more preferably 5 to 20 nm.
• the lower electrode 11 may be transparent or may not be transparent and may reflect light.
• the material constituting the lower electrode 11 include tin oxide (ATO, FTO) doped with antimony or fluorine, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO).
• conductive metal oxides metals such as gold, silver, chromium, nickel, titanium, tungsten, and aluminum; conductive compounds such as oxides or nitrides of these metals (e.g., titanium nitride (TiN), etc.); mixtures or laminates of metals and conductive metal oxides; organic conductive materials such as polyaniline, polythiophene, and polypyrrole; carbon materials such as carbon nanotubes and granphene.
• the method for forming the electrode can be selected as appropriate depending on the electrode material. Specifically, wet methods such as printing methods and coating methods; physical methods such as vacuum evaporation methods, sputtering methods and ion plating methods; and chemical methods such as CVD and plasma CVD methods can be mentioned.
• wet methods such as printing methods and coating methods
• physical methods such as vacuum evaporation methods, sputtering methods and ion plating methods
• chemical methods such as CVD and plasma CVD methods
• CVD and plasma CVD methods can be mentioned.
• the material of the electrode is ITO, methods such as electron beam method, sputtering method, resistance heating vapor deposition method, chemical reaction method (sol-gel method, etc.), and coating of indium tin oxide dispersion can be used.
• the photoelectric conversion element preferably has one or more intermediate layers in addition to the photoelectric conversion film between the conductive film and the transparent conductive film.
• the intermediate layer include a charge blocking film. If the photoelectric conversion element has this film, the characteristics (photoelectric conversion efficiency, response speed, etc.) of the resulting photoelectric conversion element will be better.
• the charge blocking film include an electron blocking film and a hole blocking film.
• the electron blocking film is a donor organic semiconductor material (compound), and the above p-type organic semiconductor can be used. Additionally, polymeric materials can also be used as the electron blocking film. Examples of the polymeric material include polymers such as phenylene vinylene, fluorene, carbazole, indole, pyrene, pyrrole, picoline, thiophene, acetylene, and diacetylene, and derivatives thereof.
• the electron blocking film may be composed of a plurality of films.
• the electron blocking film may be composed of an inorganic material.
• inorganic materials have a higher dielectric constant than organic materials, so when an inorganic material is used for an electron blocking film, more voltage is applied to the photoelectric conversion film, increasing photoelectric conversion efficiency.
• Inorganic materials that can be used as electron blocking films include, for example, calcium oxide, chromium oxide, copper chromium oxide, manganese oxide, cobalt oxide, nickel oxide, copper oxide, copper gallium oxide, copper strontium oxide, niobium oxide, molybdenum oxide, and indium oxide. Copper, indium silver oxide and iridium oxide may be mentioned.
• the hole blocking film is an acceptor organic semiconductor material (compound), and the above n-type organic semiconductor can be used. Note that the hole blocking film may be composed of a plurality of films.
• Examples of the method for manufacturing the charge blocking film include a dry film forming method and a wet film forming method.
• Examples of the dry film forming method include a vapor deposition method and a sputtering method.
• the vapor deposition method may be either a physical vapor deposition (PVD) method or a chemical vapor deposition (CVD) method, and a physical vapor deposition method such as a vacuum vapor deposition method is preferable.
• Examples of wet film forming methods include inkjet method, spray method, nozzle printing method, spin coating method, dip coating method, casting method, die coating method, roll coating method, bar coating method, and gravure coating method. In terms of patterning, the inkjet method is preferred.
• each charge blocking film is preferably 3 to 200 nm, more preferably 5 to 100 nm, and even more preferably 5 to 30 nm.
• the photoelectric conversion element may further include a substrate.
• the substrate include a semiconductor substrate, a glass substrate, and a plastic substrate. Note that the position of the substrate is such that a conductive film, a photoelectric conversion film, and a transparent conductive film are usually laminated in this order on the substrate.
• the photoelectric conversion element may further include a sealing layer.
• the performance of photoelectric conversion materials may deteriorate significantly due to the presence of deterioration factors such as water molecules. Therefore, the entire photoelectric conversion film is covered with a sealing layer made of dense ceramics such as metal oxide, metal nitride, or metal nitride oxide, or diamond-like carbon (DLC), which does not allow water molecules to penetrate. The above deterioration can be prevented by sealing.
• Examples of the sealing layer include those described in paragraphs [0210] to [0215] of JP-A-2011-082508, the contents of which are incorporated herein. Below, the form of each layer constituting the photoelectric conversion element of the second embodiment of the present invention will be explained in detail.
• the photoelectric conversion element of the second embodiment is a photoelectric conversion element having a conductive film, a photoelectric conversion film, and a transparent conductive film in this order, and the photoelectric conversion film contains the specific compound 2.
• the photoelectric conversion film is the same as the photoelectric conversion element of the first embodiment except that it contains specific compound 2 instead of specific compound 1, and the preferred range is also the same.
• the photoelectric conversion element of the second embodiment has an electrode and a charge blocking film (e.g., an electron blocking film, a hole blocking film, etc.) that the photoelectric conversion element of the first embodiment can have. Good too.
• specific compound 1 in the photoelectric conversion element of the first embodiment may be replaced with “specific compound 2.”
• specific compound 2 For example, the statement “The molecular weight of specific compound 1 is preferably 400 to 1,200” may be read as “the molecular weight of specific compound 2 is preferably 400 to 1,200.”
• the photoelectric conversion element of the second embodiment has a photoelectric conversion film.
• the photoelectric conversion film contains specific compound 2.
• D 2 A 2 (2)
• a 2 represents a group represented by any one of formulas (A-1) to (A-4).
• D 2 represents a group represented by formula (D-2).
• R W41 represents a hydrogen atom or a substituent.
• R Z41 to R Z43 each independently represent a hydrogen atom or a substituent.
• R W41 a hydrogen atom is preferable. When there is a plurality of R W41s , the R W41s may be the same or different.
• D 2 represents a group represented by formula (D-2).
• Ar d21 represents a group represented by formula (Ar-1).
• R d21 to R d23 each independently represent a hydrogen atom or a substituent.
• n d21 represents an integer from 0 to 5.
• the group represented by formula (Ar-1) has the same meaning as the group represented by formula (Ar-1) as Ar d11 , and the preferred embodiments are also the same.
• R d21 to R d23 and n d21 have the same meanings as R d11 to R d13 and n d11 in formula (D-1), respectively, and preferred embodiments are also the same.
• Z 11 , Z 12 , Z 21 , Z 22 , Z 31 , Z 41 and Z 42 are preferably oxygen atoms or sulfur atoms.
• Examples of the specific compound 2 include the following compounds.
• An example of a use of a photoelectric conversion element is an image sensor.
• An image sensor is an element that converts optical information of an image into an electrical signal.
• multiple photoelectric conversion elements are arranged on the same plane in a matrix, and each photoelectric conversion element (pixel) converts an optical signal into an electrical signal.
• pixel converts an optical signal into an electrical signal.
• each pixel is composed of one or more photoelectric conversion elements and one or more transistors.
• the photoelectric conversion element of the present invention is preferably used as an optical sensor.
• the above photoelectric conversion element may be used alone, or may be used as a line sensor in which the above photoelectric conversion elements are arranged in a straight line, or as a two-dimensional sensor in which the above photoelectric conversion elements are arranged on a plane.
• the present invention also includes inventions of compounds.
• the compounds of the present invention are Specific Compound 1 and Specific Compound 2.
• 3,4-Pyridinedicarboxylic anhydride (3 g, 20 mmol), acetic anhydride (30 mL), triethylamine (5.6 mL, 40 mmol) and tert-butyl acetoacetate (3.3 mL, 20 mmol) were mixed and heated at room temperature for 24 hours. Stirred. Acetic anhydride was distilled off under reduced pressure to obtain an intermediate. Next, water (18 mL) and 30% by mass aqueous hydrochloric acid solution (12 mL) were added, and the mixture was stirred at room temperature for 1 hour.
• a photoelectric conversion element (A) having the form shown in FIG. 2 was produced using the obtained compound.
• the photoelectric conversion element includes a lower electrode 11, an electron blocking film 16A, a photoelectric conversion film 12, a hole blocking film 16B, and an upper electrode 15.
• amorphous ITO is formed into a film by sputtering on a glass substrate to form a lower electrode 11 (thickness: 30 nm), and the following compound C-1 is further vacuum-heated and vapor-deposited on the lower electrode 11.
• An electron blocking film 16A (thickness: 30 nm) was formed by a method.
• each specific compound and an n-type organic semiconductor were deposited on the electron blocking film 16A to a thickness of 80 nm in terms of a single layer by vacuum evaporation.
• a film was formed by co-evaporation.
• a photoelectric conversion film 12 having a bulk heterostructure of 160 nm (240 nm when a p-type organic semiconductor material was also used) was formed.
• the film formation rate of the photoelectric conversion film 12 was The speed was set at 1.0 ⁇ /sec.
• the following compound C-2 was deposited on the photoelectric conversion film 12 to form a hole blocking film 16B (thickness: 10 nm).
• Amorphous ITO was deposited on the hole blocking film 16B by sputtering to form the upper electrode 15 (transparent conductive film) (thickness: 10 nm).
• an SiO film as a sealing layer on the upper electrode 15 by a vacuum evaporation method
• an aluminum oxide (Al 2 O 3 ) layer is formed thereon by an ALCVD (Atomic Layer Chemical Vapor Deposition) method to form a photoelectric conversion element. (A) was produced.
• the dark current of each of the obtained photoelectric conversion elements (A) was measured by the following method. A voltage was applied to the lower electrode and upper electrode of each photoelectric conversion element (A) so that the electric field strength was 2.5 ⁇ 10 5 V/cm, and the current value in the dark (dark current) was measured. . As a result, it was found that all photoelectric conversion elements had a dark current of 50 nA/cm 2 or less, indicating a sufficiently low dark current.
• the photoelectric conversion elements (A) of each Example and each Comparative Example had a photoelectric conversion efficiency of 40% or more at a wavelength of 560 nm, and had an external quantum efficiency of a certain level or more as a photoelectric conversion element.
• each photoelectric conversion element (A) obtained was evaluated.
• a voltage was applied to each photoelectric conversion element to have an intensity of 2.0 ⁇ 10 5 V/cm.
• an LED light emitting diode
• the photocurrent at a wavelength of 560 nm is measured with an oscilloscope, and it is determined to be 0 (at the time of no irradiation). ) to 97% signal strength was measured.
• the rise time of the photoelectric conversion element of Example 1-1 is normalized to 1
• the rise time of each photoelectric conversion element (A) is determined, and each photoelectric conversion element is calculated based on the rise time.
• the responsiveness of the conversion element (A) was evaluated according to the following evaluation criteria. AA: Less than 0.9 A: 0.9 or more and less than 2.0 B: 2.0 or more and less than 3.0 C: 3.0 or more and less than 4.0 D: 4.0 or more and less than 5.0 E: 5. 0 or more
• the above evaluation result is preferably C or more, and most preferably AA.
• Photoelectric conversion elements (B) of each Example and each Comparative Example were produced in the same manner as the photoelectric conversion element (A) except that the deposition rate of the photoelectric conversion film 12 was 3.0 ⁇ /sec. Using the obtained photoelectric conversion element (B), the photoelectric conversion efficiency (external quantum efficiency) was evaluated in the same manner as shown in the item [Evaluation of photoelectric conversion efficiency (external quantum efficiency)]. .
• the photoelectric conversion element of the present invention has excellent manufacturing suitability. It was confirmed that both photoelectric conversion efficiency and responsiveness were better when the photoelectric conversion film further contained an n-type organic semiconductor and a p-type organic semiconductor (Examples 1-1 to 1-13).

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